This invention is directed to novel quaternary ammonium siloxane compounds and their preparation. These compounds are useful as general antimicrobial agents. In particular the compounds are useful in ophthalmic compositions as disinfecting and/or preserving agents. The invention is also directed to methods for using the compounds, particularly in ophthalmic compositions where antimicrobial activity is desired.
The antimicrobial activity of some quaternary ammonium compounds is known; see for example, Petrocci et al., Dev. Ind. Micro., 20, Chapter 1 (1978); Petrocci, Disinfection, Sterilization and Preservation, Third Edition, Chapter 14 (1983); Hugo et al., Principles and Practice of Disinfection, Preservation and Sterilization, Chapter 2 (1982). In addition, some polymeric quaternary ammonium compounds have also been found to exhibit antimicrobial activity; see Hoover, J. Macromolo. Sci.-Chem., A4 (6) pp. 1327-1417 (October 1970); Rembaum, Applied Polymer Symposium, No. 22, 299-317 (1973).
Silanyl and siloxane compounds have been disclosed for their antimicrobial properties in U.S. Pat, No. 4,259,103 issued to Malek et al.; U.S. Pat. No. 4,614,675 issued to Ona et al. and U.S. Pat. No. 3,794,736 issued to Abbott et al.
U.S. Pat. Nos. 4,587,321 and 4,533,71 4, both issued to Sebag et al. disclose quaternary ammonium siloxane polymers. These patents do not disclose the compounds of the present invention which are siloxane quaternary ammonium compounds, some of which are polymeric siloxane quaternary ammonium compounds.